Crossdresser/Transgender Books That You’ll Find Helpful

Crossdressing and Transgender Books are significant ways to increase our understanding of one’s gender identity and the crossdressing/transgender community.

These books include helpful tips for us crossdressers and transgender people alike, giving insights into the transition journey. Various books touch on the transgender and crossdressing community, specifically gender identity, transitioning, crossdressing, and the conflicts in realizing one’s true identity. By reading these books, we will better understand the community, the transgender people, cross-dressing people, and the struggles we unknowingly face.

There are not enough stories written by transgender/crossdressing authors. It is important to acknowledge that our lives aren’t always perfect. These stories depict how we, as crossdressers/transgender, have existed throughout history and will continue to do so into the future. The reality of these stories helps us acknowledge how challenging transitions and identities can be, whether it be with our loved ones or on a personal and physical level.

We want other crossdressers/transgender who identifies as a member of this community, to know that there might not be a one-size-fits-all narrative that follows behind them when they come out. Instead, they deserve experiences that embrace all their tender complexities while also including others in this space of gender identity and sexual orientation.

At times, all we want is to be seen. Visibility is not just about being heard or seen but about seeing authentic and expansive representations of who we are. Through these books, other people can depict our lives as we see them: beautiful, joyful, and without confines.

1. My Journey: Sally to Shay by Shay Robertson

In his intensely personal and creatively written book, My Journey: Sally to Shay, author Shay Robertson lays out the various stages of his transition from female to male. In this astonishing and touching tale of a man’s struggles to find himself and overcome insurmountable odds, Robertson takes readers year by year through his amazing journey as he realizes not only who he was but also what kind of man he wanted to be. This profoundly insightful story is a must-read for anyone considering transitioning or questioning their own gender identity and is an invaluable guide for anyone looking to support or counsel those they love on their own journeys in the same way that Robertson largely credits his wives, family members, and friends with helping him realize the Shay he wanted to become.

My Journey: Sally to Shay by Shay Robertson describes in detail the situations that occurred during his transition of becoming a man. On the one hand, there are times when he finds his transition to be funny, sad, informative, and inspiring. Everything is in such a manner that no one would think twice about it. On the other hand, there are also awkward moments to handle, like when you’re out as a woman and end up having very life-changing results like surgeries and medication. This book is full of events that may leave you stunned and inspired at all levels.

2. My Husband Betty by Helen Boyd

My Husband Betty – written by the wife of a male transgender transitioning to female was mainly created as an explanatory tool for spouses, partners, and loved ones interested in learning more about transgenderism. It goes much deeper than this, providing helpful suggestions and general information concerning trans people of all types. The author takes on much of the controversy surrounding sexuality and gender identity with honesty, willingness, and sometimes even doubt (after all, she is only human) but ensures us that regardless of her personal opinions, she will always let us know when she’s being subjective. In order to make use of this resource, it is important to read from front to back rather than jumping around between topics or specific goals; otherwise, one risks losing valuable information.

Helen explains what she has learned from both personal experiences and five years of research. Also, she shows readers how some MTF crossdressers and why women, their partners or wives, choose to stay with them. She describes six couples from her online support group and shows many ways of dealing with cross-dressing relationships. 

3. Transvestism and Crossdressing: Current Views by Jed Bland

Beaumont Trust’s Transvestism and Crossdressing is a fantastic collection of articles written by experts in their field; these are written by professional writers sharing advice and information about this often misunderstood topic. The book provides an intelligent and very well-written approach to one of the most prevalent issues currently facing transgender and crossdressing individuals worldwide. It discusses everything from labels and definitions to being in the closet, cultural history, law, and counseling and support for those dealing with these issues.

This book explains why some men are curious about wearing female clothes or are actually seeking women’s underwear, never having dressed in this way until they were adults. These issues, touching such aspects of human sexuality, have been sometimes neglected by others. By answering some of the most common questions about crossdressing in more detail than is possible but still being non-directive and non-judgmental, it provides answers that help to satisfy curiosity and enable readers to learn a lot more about what crossdressing is all about.

4. Stuck in the Middle with You: A Memoir of Parenting in Three Genders by Jennifer Finney Boylan

In a brief time span in between, neither, or both, Boylan has seen parenthood from all sides of the gender divide. From being a doting father for six years to becoming a mother for ten. When her two young children were growing up at home, she came out as transgender. Still, when her family faced challenges because of that information, she decided to stay on course and see through the transition and become a fully realized woman. The most challenging part about this was simply facing society’s lack of understanding of accepting gender fluidity into mainstream culture. As one who grew up so comfortably as a male from childhood into young adulthood before feeling an insurmountable urge to shed everything that came with being appreciated as female, Boylan knows firsthand what it feels like to wade through gender categorization norms and prejudices in order to grow unabashedly as an individual.

Parenting is challenging under any circumstances, and transgender parents face an even more challenging road. Jennifer Finney Boylan’s new book Stuck in the Middle with You relates the story of a family as they struggle to come together and do what’s best for all involved – one that openly discusses the challenges faced by transgender parents with warmth, sensitivity, and positivity.

5. Introducing Teddy: A story about being yourself by Jessica Walton

Introducing Teddy by Jessica Walton is a story that portrays being true to yourself, loving your friends, and being a best friend to the people around you. This book follows Errol and his teddy, who have been together since they were babies. Even before Errol was born, Thomas knew he wanted to be friends with him. They do everything together, but Errol realizes there’s something different about his best pal. But what could it be? This story is an important reminder for kids about acceptance and being good to their friends no matter what!

This is a tale that tells us all not to be afraid to be who we are – no matter who or what we are; because, like Thomas, the teddy, points out, it’s important to be true to ourselves regardless of gender. Errol and Thomas are best friends in the book, but one day Thomas feels like she wants to say something: ‘In my heart, I’ve always known that I’m a girl teddy, not a boy teddy. But I can’t bring myself to tell you.’ And Errol says, ‘I don’t care if you’re a girl teddy or a boy teddy! What matters is that you are my friend.‘ Here, the audience learns that gender identity does not necessarily mean sexual orientation but rather what one identifies with on the inside regardless of how anyone else perceives them.

6. Gender Born, Gender Made: Raising Healthy Gender-Nonconforming Children by Diane Ehrensaft, Ph.D

Gender Born, Gender Made: Raising Healthy Gender Non-Conforming Children by Diane Ehrensaft, Ph.D., tells people how one should never be judged about what gender they identify as. This book offers parents and educators tips for dealing with the challenges of helping a child who doesn’t quite fit into a typical gender mold become their most authentic self without putting too much pressure on them to conform. She offers scathing criticism of the outdated theories that may actually be harming children and suggests new ways to approach these complex issues in this comprehensive guide aimed at both professionals and those raising gender nonconforming children.

It’s nice to know that there are people out there making sure that the next generation doesn’t have to experience the same discrimination based on their choices when it comes to gender. Everyone can learn from a book like this, and more children in the future will get to be whoever they want to be without restrictions or obligations, so they can just do themselves being whoever they want with no limits or boundaries!

The books listed here will touch on the reasons why we, as crossdressers and transgenders do what we do, the struggles, and the types of treatment our community receives from society. These books will answer many questions that a reader may have about a crossdresser and transgender person.

Whether you’re looking for self-improvement or some inspiration in your life, you’re sure to find it within one of these titles! Celebrate and be inspired by the lives and works of numerous crossdressing, transgender, non-binary, and gender-nonconforming authors by reading their compelling stories on this list.